Oak Street Tours and Activities

Photo by Eleonora Bertacchi
Photo by Eleonora Bertacchi

Plan a trip to see Oak Street

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$828, price is now AU$565 per person
AU$565
per person
16 Nov - 19 Nov
found 4 hours ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
I wish that all the staff was more accommodating! some of them were some were not!

Reviewed on 6 Oct 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
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Price was AU$1,857, price is now AU$1,166 per person
AU$1,166
per person
16 Nov - 19 Nov
found 4 hours ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on 6 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,186, price is now AU$762 per person
AU$762
per person
16 Nov - 19 Nov
found 4 hours ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on 7 Oct 2025

Tours & day trips

See all 152 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour and 15 minutes
9.6 out of 10 with 1482 reviews
Free cancellation available
Price is AU$74 per adult
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Food, drink & nightlife

See all 25 activities
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

Activity duration is 1 hour and 30 minutes
9.0 out of 10 with 20 reviews
Free cancellation available
Price is AU$64 per adult
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Private & custom tours

See all 24 activities
Eastside Chicago The Heist Exploration Game and Tour

Eastside Chicago The Heist Exploration Game and Tour

Activity duration is 1 hour and 35 minutes
Free cancellation available
Price is AU$14 per adult*
Eastside Chicago The Heist Exploration Game and TourOpens in new tab

Attractions

See all 16 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 30 minutes
8.4 out of 10 with 671 reviews
Free cancellation available
Price is AU$46 per adult
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Adventure & outdoor

See all 12 activities
Chicago: Two Flight Indoor Skydiving Experience

Chicago: Two Flight Indoor Skydiving Experience

Activity duration is 1 hour
10.0 out of 10 with 1 review
Free cancellation available
Price is AU$156 per traveller
Chicago: Two Flight Indoor Skydiving ExperienceOpens in new tab

Popular places to visit

900 North Michigan Shops

900 North Michigan Shops

You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

900 North Michigan Shops
Fourth Presbyterian Church

Fourth Presbyterian Church

Fourth Presbyterian Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Fourth Presbyterian Church
875 North Michigan Avenue

875 North Michigan Avenue

You can find out about the history of Chicago when you stop by John Hancock Center. Amble around this vibrant area's lakeside or experience its fascinating museums.

875 North Michigan Avenue
Washington Square

Washington Square

Learn about the local history of Chicago with a stop at Washington Square. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Washington Square
Oak Street Beach

Oak Street Beach

Why not spend a care-free afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Oak Street Beach
Chicago Water Tower

Chicago Water Tower

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Chicago Water Tower

Top Oak Street Hotel & Accommodation Deals

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Congress Plaza Hotel
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl, Chicago, IL
The Whitehall Hotel, BW Premier Collection
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Freehand Chicago
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Warwick Allerton - Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Hilton Garden Inn Chicago Downtown/Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street, Chicago, IL
The Chicago Hotel Collection - Magnificent Mile
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
InterContinental Chicago Magnificent Mile by IHG
See all 4,048 properties in Oak Street
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.